Method for synthesizing melonal

A technology of melon and formaldehyde, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve the problems of high COD wastewater, high acid-base unit consumption, complex process flow, etc. High rate, simplified operation, simple operation effect

Active Publication Date: 2022-04-08
WANHUA CHEM GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of high-efficiency synthetic method of melon aldehyde, take easy-to-get 5-methyl-1,4-hexadiene as starting material as raw material, through hydroformylation, aldol condensation and selective Melon aldehyde is obtained by reactions such as hydrogenation. The method of the invention is simple, the conditions are mild, the raw materials are cheap and easy to obtain, and it has good potential application value; it solves the problem of large acid-base unit consumption and high COD waste water in the existing synthesis process of melon aldehyde. , complex process and other issues

Method used

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  • Method for synthesizing melonal

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Effect test

Embodiment 1

[0041] Rhodium-catalyzed hydroformylation of 5-methyl-1,4-hexadiene to 6-methyl-5-heptenal.

[0042] In the glove box, weigh [Rh(acac)(CO) 2 ] (89mg, 0.25mmol), 1,2-bis(diphenylphosphine)ethane (113mg, 0.28mmol) and tricyclohexylphosphine (154mg, 0.55mmol) were placed in a single-necked flask with a magnetic stir bar , Then add the solvent toluene (30mL), after the single-necked flask is sealed, after stirring and coordinating at room temperature for 20 minutes, take it out from the glove box. Under the protection of a nitrogen balloon, the catalyst solution was pumped into a 250mL autoclave with an advection pump. The autoclave had been replaced with nitrogen and synthesis gas three times in advance. The autoclave was filled with synthesis gas and the pressure was normal pressure. After the catalyst solution is fed, start stirring, then put the raw material 5-methyl-1,4-hexadiene (48.1g, 0.5mol) and the solvent toluene (70mL) into the autoclave, and finally fill the reaction...

Embodiment 2

[0044] Rhodium-catalyzed hydroformylation of 5-methyl-1,4-hexadiene to 6-methyl-5-heptenal.

[0045] In the glove box, weigh [Rh(acac)(CO) 2 ] (21mg, 0.06mmol), 1,2-bis(diphenylphosphine)ethane (72mg, 0.18mmol) and tricyclohexylphosphine (50mg, 0.18mmol) were placed in a single-necked flask with a magnetic stir bar , Then add the solvent toluene (30mL), after the single-necked flask is sealed, after stirring and coordinating at room temperature for 20 minutes, take it out from the glove box. Under the protection of a nitrogen balloon, the catalyst solution was pumped into a 250mL autoclave with an advection pump. The autoclave had been replaced with nitrogen and synthesis gas three times in advance. The autoclave was filled with synthesis gas and the pressure was normal pressure. After the catalyst solution is fed, start stirring, then put the raw material 5-methyl-1,4-hexadiene (57.7g, 0.6mol) and the solvent toluene (70mL) into the autoclave, and finally fill the reaction k...

Embodiment 3

[0047] Rhodium-catalyzed hydroformylation of 5-methyl-1,4-hexadiene to 6-methyl-5-heptenal.

[0048] In the glove box, weigh [Rh(acac)(CO) 2 ] (107mg, 0.3mmol), 1,2-bis(diphenylphosphine)ethane (131mg, 0.33mmol) and tricyclohexylphosphine (93mg, 0.33mmol) were placed in a single-necked flask with a magnetic stir bar , Then add the solvent toluene (30mL), after the single-necked flask is sealed, after stirring and coordinating at room temperature for 20 minutes, take it out from the glove box. Under the protection of a nitrogen balloon, the catalyst solution was pumped into a 250mL autoclave with an advection pump. The autoclave had been replaced with nitrogen and synthesis gas three times in advance. The autoclave was filled with synthesis gas and the pressure was normal pressure. After the catalyst solution is fed, start stirring, then put the raw material 5-methyl-1,4-hexadiene (28.9g, 0.3mol) and the solvent toluene (50mL) into the autoclave, and finally fill the reaction ...

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Abstract

The invention provides a method for synthesizing melonal. The method comprises two steps of reactions: S1, 5-methyl-1, 4-hexadiene is subjected to a hydroformylation reaction, and a 6-methyl-5-heptenal intermediate is obtained; and S2, carrying out one-pot condensation on 6-methyl-5-heptenal, paraformaldehyde or formaldehyde and hydrogen, and carrying out hydrogenation to obtain the melonal product. The synthetic route is novel, the melonal is obtained with high yield by starting from simple and easily available raw materials through two-step reaction, and the method is simple to operate and high in yield and has better advantages. Secondly, in the hydroformylation reaction, a monophosphine ligand and a diphosphine ligand are matched for use, so that side reactions such as raw material hydrogenation and product hydrogenation are effectively reduced. And finally, in condensation and hydrogenation reactions, related conversion is completed by using a one-pot method, and tertiary amine and Lewis acid are used for concerted catalysis, so that the operation is simplified, and the product yield is improved.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a method for synthesizing melon aldehyde. Background technique [0002] Melon aldehyde, scientific name 2,6-dimethyl-5-heptenal, is a light yellow oily liquid at room temperature, with a strong, fresh melon fragrance. Melon aldehyde is a food flavor allowed by the national standard, and can be used to prepare melon, cucumber and tropical fruit flavors. The chemical properties of melon aldehyde are relatively active, soluble in organic solvents such as ethanol and propylene glycol, but insoluble in water; melon aldehyde naturally exists in essential oils such as citronella oil, but the content is low, and the extraction cost is expensive. Mainly synthetic. [0003] According to literature reports, the classic synthesis method of melon aldehyde is to use methyl heptenone as a raw material, undergo Darzens condensation with chloroacetate to obtain an epoxy intermediate, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C45/75C07C47/21
Inventor 黄文学吴珍珍王新伟闫化莲曲淑玲韩鑫黎源
Owner WANHUA CHEM GRP CO LTD
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